Ethyl Acetate → HCID 22016838, compound

HRID 1871193Notes

Reaction equation

HRID 1871193 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])#[N:2].[BH4-].[Li+].CCOC(C)=O>C1COCC1.Cl>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[O:13][CH3:14])#[N:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 22464400Methyl 4-cyano-3-methoxybenzoate

Product 1

HCID 22016838HCID 22016838, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ester from Step D (48.8 g, 255 mmol) in 400 mL of dry THF under argon at room temperature was added lithium borohydride (255 mL, 510 mmol, 2M THF) over 5 minutes. After 1.5 hours, the reaction was warmed to reflux for 0.5 hours, then cooled to room temperature. The solution was poured into EtOAc/IN HCl soln. [CAUTION], and the layers were separated. The organic layer was washed with water, sat Na2CO3 soln. and brine (4x), dried (Na2SO4), and concentrated in vacuo to provide the titled product (36.3 g, 87% yield).

Workup

  1. temperaturethe reaction was warmed
  2. temperatureto reflux for 0.5 hours
  3. custom[CAUTION], and the layers were separated
  4. washThe organic layer was washed with water
  5. dry with materialand brine (4x), dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c12ef83b1dd84ef79d675698d3364fd1
Source dataset
uspto-grants-2000_08
Patent number
US06103487

Reaction notes

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